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It's not the largest denomination, but the $20 bill holds a very special place in our hearts and wallets. Maybe it's because it's what people in heists always request? (Non-sequential.) Maybe it's because $20 is the highest denomination you can whip out without causing eye rolls? Or maybe it's because it's the perfect amount to wager with a friend: high enough to raise the stakes, low enough not to devastate whomever loses.

Did you know, on average, a $20 bill lasts only four years in circulation? True story. If you don't believe me, check if any of the $20 bills below have recently been buried in your wallet. (They haven't. Which makes 'em even cooler.)

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1928

For whatever reason, they swapped out Cleveland for Jackson. No one seems to be sure why, and the reserve won't reveal why. This is also the first year of the small-sized note, which replaced the preceding bills that were about an inch taller and wider.

The White House also made the back for the first time, probably because the White House couldn't evolve, like a train or ship.

1929

The banners up top are gone, replaced by straight text. The issuing Federal Reserve Bank is given a non-circular treatment. It also gets rid of the "on demand" aspect of the bill, meaning it will not give you gold if you ask for it. Ugh, jerks. No wonder this happened in October.

1942

With WWII raging in the Pacific, a special emergency series of money was over-printed, with Hawaii labeled on it so that if the Japanese captured the island, the money they seized would be worthless. (This bill is from 1934 and was part of a different series, but that's what the printing looked like.)

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1963

Remember how they replaced the very changeable transportation methods with the static White House? Well, they had to update the back of the bill when it was remodeled. They added a balcony and the trees grew, and the bill had to catch up with the times. The probably unconstitutional "In God We Trust" also snuck onto the bill.